


Bert and Ernie

by LustDemonRosier



Category: Supernatural
Genre: Angst, Blow Jobs, M/M, Sex in the Impala, Sexual Inexperience
Language: English
Status: Completed
Published: 2013-09-02
Updated: 2013-09-02
Packaged: 2017-12-25 10:16:30
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,741
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/951901
Author URL: https://archiveofourown.org/users/LustDemonRosier/pseuds/LustDemonRosier
Summary: <blockquote class="userstuff">
              <p>Obligatory and shameless fangirling over episode 3 of season 5 when Dean tries to help Cas lose his virginity. Never let it be said that Dean Winchester isn't a determined and creative problem solver. More angst than I can typically stand writing, but hey, I needed Dean a little vulnerable to get things going.</p>
            </blockquote>





	Bert and Ernie

**Author's Note:**

> Beta'd by Viveca. Ties into my other story "Cas' Bad Timing" but stands alone fine by itself.

Cas watched as Dean ducked inside the Impala and slammed the door shut. A minute ago he had been laughing so hard he gasped for breath but somewhere in the middle of the almost empty parking lot, between the brothel poorly disguised as a seedy strip club and Dean's beloved classic automobile, his demeanor did a one eighty. Still standing outside the car, peering thoughtfully into the darkness, he tried to work out what had caused his friend to become so serious. Then the passenger door of the car smacked him right in the crotch, making him flinch.

“Get in,” Dean ordered gruffly, leaning over the worn bench seat to open the door. The angel did as he was told, dipping into the car and folding his hands over his lap after shutting the door. Dean had straightened himself up in the driver's seat but made no move to turn the key nestled in the ignition. Cas stared forward out the windshield patiently awaiting whatever antics his friend had in store for the rest of the evening. Dean just sighed loudly, giving Cas the impression he was supposed to say or do something.

“I still do not know who Bert and Ernie are,” he deadpanned. It was a weak attempt at humor, even the angel could recognize that. Dean just snorted. “You're upset. Because I angered the prostitute.”

“No,” the hunter laughed weakly. “Just not how I planned tonight would pan out.”

“I've disappointed you,” the angel replied, venturing a glance at his friend. Dean smacked a hand on the steering wheel. As far as Castiel had been able to discern it was a demonstration of anxiousness.

“I don't know what I expected,” Dean grumbled. “It's just, well, it's the end of the world. I'm not nearly drunk enough for this shit. Sam's off God only knows where, doing God only knows what. And you're still a virgin.” He tilted his head back and slumped in the seat, running his hand through his hair like the angel had seen him do when he was worried. “The fuck am I doing?”

Cas watched the hunter quite literally wallowing in doubt and helplessness, the faintest seeds of the very human feeling of concern creeping into his psyche. Though he was less than apt at expressing himself in a manner that his human friends found sympathetic, he was more observant than they gave him credit for. He understood what the loss of his brother meant to Dean, more than the man knew, which was probably for the best, considering what had happened when Cas had stumbled unwitting into one of their romantic interludes several months ago. He forced the thought out of his mind but not nearly fast enough to keep his breath from hitching and his pants tightening a size or two.

“It's not your fault,” Cas offered. He had heard the Winchesters say it to each other, but he was not sure if it actually provided any comfort. “Sam will come back. He just needs time.”

“Not sure I even want him to,” huffed Dean, crossing his arms and refusing to look at the angel in the passenger seat. “Probably better this way.”

“Maybe.”

“You were a better shrink for the hooker, you know that?” the elder Winchester jested, smirking at Cas before he turned himself over on the bench seat and started groping around in the back seat. With his knees pressing into the driver's seat, his ass was sticking lewdly up in the air. Cas grimaced and licked his lips.

“What are you doing?” he asked, a little more breathlessly than he intended. Dean leaned down a little further, his threadbare dirty jeans pulling taut against the perfect curve of his ass, making Cas wonder how his own brother could fail to appreciate, kneel down, and worship the beauty of these creatures. Dean righted himself then, a half empty bottle of whiskey in his fist. “What are you doing?” the angel repeated, mouth strangely dry.

“We're probably going to die,” he answered with a shrug. Apparently he had come to terms with this in the thirty seconds it took him to fish the bottle out of the clutter on the floor. He was stunning with that reckless kind of resilience. No wonder his Father loved them so much, no wonder He send a squadron of angels just to pull this one incredible man out of the Pit. And Castiel thought he would happily battle the hoards of vicious, soul mangling monsters again to save him. Dean took lengthy pull of the bottle before wiping his mouth with the back of his hand. “It'll probably be tomorrow, and if it's not tomorrow then probably the next day or the day after that. And you're still a virgin.”

“I don't think my sexual inexperience is the item of most concern at the moment,” Cas objected, but Dean just thrust the bottle at him with that commanding look. The angel never had it in him to refuse him anything so he took a dainty sip.

“Yeah, but that's the only thing I have any control over,” the older Winchester responded in low voice that made something creep up the angel's spine. Dean was watching him with a strange intensity that made Castiel feel like he was being scrutinized. He swallowed down the burning liquid and took another pull, longer this time, without breaking eye contact with Dean.

“If you're suggesting we go back in the club,” Cas began uncertainly, passing the bottle back to his friend who was eying him with the kind of wolfish look he usually reserved for greasy fast food and his car. Dean helped himself to another generous slug off the bottle.

“No,” he said gruffly, capping the bottle and unceremoniously discarding in the back seat. “No, that won't work.” His voice had become distant, an odd tone that made Cas consider disappearing out of the car, but then Dean was edging toward him. He swung his denim clad legs over the console and was inches from being pressed against Cas' side in the second it took him to sort through what was happening. Then Dean grabbed his wrist and stretched with feline fluidity so his lips were teasingly close to the angel's ear.

“Don't disappear on me,” he ordered, warm breath tickling the delicate shell of the angel's ear. His voice was thick with an unfamiliar neediness and starting to slur a little from all the alcohol he had imbibed in the last couple hours. Cas slowly turned his head to face Dean completely and one of Dean's hands touched his face hesitantly while the other propped his unsteady frame up as he leaned across the seat. The angel pressed his cheek into the gentle touch, giving permission to Dean's caress. “Please don't go,” the hunter whispered, practically begged, the cloying smell of alcohol filling Cas' nose. Then he pressed his soft full lips right onto the angel's and Cas froze, shocked by disbelief and inexperience.

Dean hung there for a second with Cas motionless before him until the human pulled away and sat back stiffly against the seat. His hand fluttered nervously through his hair again for a few tense moments.

“Sorry,” he mumbled, starting to shift back to the driver's side. The movement pulled Cas back to sense and he reached out for Dean's jacket.

“No,” the angel ordered, tightening his grip and tugging a bit like a child that wanted attention. Dean cocked his head to the side, giving Cas a sideways glance that exposed his neck. Cas wanted to pepper that sweet stretch of skin with a thousand kisses, had wanted to do as much and so much more for so long. Now his first and possibly only opportunity was threatening to slip right out of his grasp. He flung himself, quick but clumsy, across the few inches that separated them. He was nearly sprawled in the hunter's lap, arms framing either side of Dean's body, hands scrabbling for a hold on the slippery upholstery for a second.

“Cas,” Dean hissed, pretty green eyes searching, so close the angel could kiss those beautiful girly eyelashes. “You really don't have to.”

“I am an angel of the Lord,” pronounced Castiel in a tone so devilish he surprised himself, “I only take orders from one source.” Then he pressed into the hunter he pulled from Perdition, his very own incredible Winchester, in a sloppy and clueless kiss and Dean reciprocated with enthusiasm. Slipping his arms under the angel's armpits, Dean gripped his shoulder blades – right where his wings would have been, Cas thought to himself – and held him close. With Cas unable to escape bodily, Dean brushed his tongue against Cas' upper lip, sweetly asking permission for entrance. The angel shuddered at the gentle sensation and obliged, letting Dean taste his tongue and the space behind his teeth. Then Dean retreated, leaving his mouth with a light peck. A pathetic whining sound squeaked in the angel's throat but Dean just chuckled and kissed his unshaved jaw.

“Just letting you catch your breath,” he laughed, little puffs of hot air bouncing off Cas' face and giving him goosebumps that spread from his neck to his shoulders and back and down his arms, making his fingers curl into the seat again. “And for future reference,” Dean muttered breathlessly against his neck, “the whole 'angel of the Lord' thing might be the worst pick-up line of all time.”

“Worked on you,” Cas gasped, feeling his dick press uncomfortably in the suddenly too small space within his trousers.

“Yeah, well, I'm easy,” Dean said and Cas could feel him smile against his neck just before nipping him under the square corner of his jaw. Then the hunter flipped them, using the leverage of his arms under Cas to pin him against the cool seat with a practiced ease and grace that almost had the angel prematurely blowing his load right then. Cas grunted, bucking his hips up involuntarily. In the dark he could see Dean smirking like he was very satisfied with himself as he flung a leg over the angel, his knee slipping between his thigh and the back of the bench seat. He had his leg all nestled into the folds of Cas' trench coat so even if the angel tried to scoot away from Dean's embrace, he couldn't get far. The angel tried to process how the man had translated all his dexterity and skill as a hunter into some kind of novel Kama Sutra for seducing angels until the hunter, still grinning like the cat who ate the canary, pressed his hardness into the angel's thigh and Cas' brain turned to mush. All that violence and fighting prowess morphed perfectly into something so arousing and sexy, like history's most perverse and erotic coping mechanism and Cas' was so utterly astonished and turned on that he hardly knew what to do with his hands, let alone the rest of his callow physical form. Dean must have sensed his bewilderment because he grabbed the hand that was dangling uselessly over the front of the seat and pressed it to his erection. Cas groaned which gave Dean the opportunity to plunge his tongue back into his mouth, his hips canting forward to rub against Castiel's open palm.

While Dean took full advantage of Cas' open and willing mouth, the hunter started undoing Cas' belt with nimble, unnervingly skillful fingers. He was making the whole process feel entirely too easy, especially with Cas' erratic squirming and bucking. Mindlessly he moved his hand from Dean's crotch to his ass and squeezed, pulling him closer until Dean was flush against his thigh and rubbing against him with mutual urgency. Dean was still kissing him dumbstruck when Cas realized he was unzipping his pants and pulling them down, making the angel moan into his mouth. Brushing his hand against the thin fabric of Cas' boxers, he got a hold of the angel's hard cock and lavished open mouthed kisses to his throat, making Cas pant and gasp now that there was no mouth sucking the noises out of him. It took him a minute to notice someone was purring Dean's name over and over and it took a few more moments to realize the needy sound was actually coming from him. He needed to get a grip or he was going to get off before they had a chance to advance beyond a little heavy petting.

“Dean,” he forced himself to say a little more firmly. Dean looked up from his neck, lips all shiny slick from the attention he was affording the angel's neck. “I, I need,” Cas struggled but suddenly his usually expansive vocabulary was restricted to the hunter's name and a few desperate, inarticulate noises. Dean seemed to understand, though, releasing the angel's painfully hard cock for a few merciful seconds. As Cas tried to steady his breathing, Dean shrugged out of his jacket. The inside of the car, which had not five minutes earlier been crispy cold, was now humid, the windows all fogged from the heat of their breath and bodies. Still Cas was shivering even though his whole vessel was on fire with a new and unfamiliar heat. Then Dean was tearing his pants and boxers down to Cas' ankles, the damp air making the angel's dick twitch as it sprung from his clothing. He watched with curiosity as a droplet of precome issued from the tip and saw that Dean was also watching, looking pleased with his handiwork.

“Isn't that a pretty sight,” said the hunter, lowering himself right between Cas' legs. “You're beautiful,” he said, nuzzling into his thigh, kissing lightly and sending a wave of pleasure through the angel's body. He kissed a lazy trail upward toward the place Cas needed him most and Cas almost lost it completely when Dean licked away the drop of glistening liquid on the head of his hardness. Cas heard himself moaning Dean's name again, his hands roving aimlessly, grasping for anything that would keep him from almost flying off the seat as Dean kissed the tip of his cock with those perfect soft lips. Nothing ever escaped Dean Winchester; with his mouth lightly sucking just the head of Cas' hard-on, he grabbed one of the angel's lost roaming hands and placed it on the back of his head, pressing Cas' hand down into his short hair. Eyes wide with arousal, he watched as his cock disappeared half-way into Dean's mouth, the hunter's pink lips curling into a smile around his dick. The sight made Cas throw his head back into the seat and suck in air. It was the most incredible scene the angel had ever witnessed – and he had been present for Creation. He wasn't going to hold out much longer.

“Wanna see a magic trick, Cas?” Dean murmured against the length of his erection, sweet little vibrations of the words coursing through his hard length. Cas made a sound of approval and forced his eyes to look at Dean, who was sucking on his index finger. For a moment the angel was baffled by where this was going, but then the hunter was licking his shaft again and Cas did not care where it was going because he knew it was going somewhere unknown but great. He felt Dean's finger reach under his sac and press, slick with his spit. The hunter's tongue was swirling over the tip of his dick and he couldn't think anymore and then he felt Dean's spit slick finger slip just a fraction of an inch into his ass and everything exploded. An unearthly, probably completely unholy, scream escaped his mouth and he couldn't stop himself from shooting his load all over Dean's swollen red lips, his cock twitching from the bolts of electric pleasure pulsing through it, traveling in waves across his whole body.

He wasn't sure how long he laid there, quaking and shuddering through his orgasm, but when he finally mustered the strength to look at his lover, he blushed with shame. Dean was still only a couple inches from his softening cock, his finger withdrawn from his tight hole and his face spattered with Cas' cum.

“Geez, Cas,” Dean muttered and absentmindedly licked a few white drops off his lips, the sight making Cas' spent dick jump in approval, “give a guy some warning next time.”


End file.
